


Going to Hell in a Handbasket

by RosalindInPants



Category: The Great Library Series - Rachel Caine
Genre: BDSM, M/M, Masturbation, Oral Sex, Teenage Fantasies, Terrible Humor, bad power dynamics, characters making questionable decisions about sex, crack ships, sin - Freeform, sinful sinful sin
Language: English
Status: Completed
Published: 2020-02-28
Updated: 2020-02-28
Packaged: 2021-02-28 07:20:23
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 2,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22940074
Author URL: https://archiveofourown.org/users/RosalindInPants/pseuds/RosalindInPants
Summary: A collection of sinful reposts from Tumblr. Read the tags. It is exactly what it says it is.
Relationships: Christopher Wolfe/Dario Santiago/Jess Brightwell, Christopher Wolfe/Niccolo Santi/Dario Santiago, Dario Santiago/Niccolo Santi, Jess Brightwell/Christopher Wolfe
Comments: 2
Kudos: 3





	1. A Followup to Chapter 1 of the Sin Collective

**Author's Note:**

  * Inspired by [Sin Collective](https://archiveofourown.org/works/21268898) by [TheGreatLibraryFangirl (Mazeem)](https://archiveofourown.org/users/Mazeem/pseuds/TheGreatLibraryFangirl). 

**Summary for the Chapter:**

> This is a follow-up to Mazeem's first Sin Collective chapter. There is no sex in this one, but there are references to sex. Warnings:  
> Wolfe/Jess and Dario/Santi  
> References to BDSM activities that were probably a very bad idea and conducted without proper regard for safety or power dynamics.  
> Terrible humor.  
> Read at your own risk.
> 
> AU: Morgan Lives (I wrote it before Sword and Pen, what can I say?)

By the time he got home, Santi was about sick with dread. Chris was going to be furious when he confessed what he had just done with Dario. There was not even a chance of hiding it. Chris knew him too well. If he didn’t confess to his sins, his beloved was going to think something far worse was wrong. He didn’t really want to think about how few such things there were.

He opened the door to a brightly-lit room. Fuck. Chris was having trouble sleeping, and here he was coming home after -

He froze. Blinked. Rubbed his eyes and looked again.

Christopher Wolfe sat at the table with a book and a cup of tea. That was hardly unusual. But on the couch…

Jess Brightwell lay on the couch, his sides rising and falling in the peaceful rhythm of sleep. He appeared to be undressed beneath the blanket that covered him.

“Well? Are you going to stop staring and come in? You’re letting the flies in.”

Santi stepped through the doorway. Closed the door behind him. Took another long look at Jess Brightwell. He’d rolled in his sleep, and the blanket slipped to reveal the long stroke of a whip mark on his back.

“Morgan brought him over,” Chris said, deceptively casual. “She wanted a lesson in that special technique of mine and had the good sense to come to an expert. Oh, do sit down, Nic. Have some tea.” He gestured to the teapot and the empty cup on the table.

“And you…?” He couldn’t finish that thought. After all Christopher’s rants about how his former students were still children, it was simply too unbelievable. “Where is Morgan?” he asked instead.

Chris took a sip of tea and looked fondly over at Jess. “She had a date, so she left him in my care. She was good enough to give me a few suggestions on how to tend to him.” He grinned, eyes alight with the sort of devious amusement he only showed after…

“Chris…” Santi said slowly, with the feeling that he was walking into a minefield. “What did you do….?”

“Oh, stop it, Nic. You know perfectly well what I did. It wasn’t so difficult when I closed my eyes and imagined he was you. As it turns out, he’s quite good with his mouth.”

Santi’s jaw dropped. He looked from Christopher’s smug grin to Jess Brightwell’s slumbering form. He poured himself a cup of tea and took a long drink. Took a deep breath. “So… while I was at the dungeon tonight…”

“You fucked Dario. Oh, stop looking at me like that. You think Khalila and Morgan don’t know how to send each other Codex messages?”

That was both a relief and a whole new source of dread. Still struck dumb, he finished his cup of tea.

“I would have thought,” Chris went on, “That you would be happier to hear me concede that you were right, my dear.”

Well, that wasn’t a regular occurrence. Pleasant as the words were to hear, he wasn’t entirely certain he followed his lover’s point. “Yes…” he said, slowly, fishing for some clue. God, he was too tired to think.

“The children are grown now, and we need to learn to relate to them as equals, not as parents. Though perhaps we have both taken a step too far in that direction tonight, hmm?” Chris stood and offered Santi his hand. “Come to bed, my love. We can torment ourselves with the implications of our sins in the morning.”

Santi took his partner’s hand and followed him toward the bedroom. When they reached the door, he looked back over his shoulder at Jess. “What about…?”

“Morgan will be by to collect him after her date. Don’t worry. She still has the spare key.” Chris gave his hand another tug. “Come. We may have had our separate adventures tonight, but the only one I want to fall asleep beside is you, dear Nic.”

Santi was only too glad to follow him.


	2. Going to Hell in a Red Robe

**Summary for the Chapter:**

> Because once I started thinking about both Wolfe and Dario wearing red robes, things happened.  
> Warnings:  
> Wolfe/Santi/Dario (this is post-canon, so everyone involved is an adult and capable of making their own very questionable choices)  
> Questionable power dynamics  
> Rope bondage  
> Vaguely described sex  
> Read at your own risk.
> 
> AU: Morgan lives (written before Sword and Pen - guess which death I didn't predict?)

Santi hadn’t planned to ever lay a finger on Dario ever again. He had gone to confession, absolved himself of his sins, and sworn to never sin again.

And then Dario showed up at their door looking both sexy and forlorn. Khalila was out of town. Jess was out of town. Even Morgan was out of town. There was no one else to send him to. No one Santi could trust, at any rate. It would be cruel to leave him to the mercies of drunk and horny soldiers in the Hive, crueler still to let him go down to the less public bar below in such a state. So he invited the boy in.

Just for a few drinks. Just to get him calmed down and put safely to bed in the spare room.

But then Dario started asking pointed questions about rope suspension, and Chris started answering those questions, and before Santi could protest, he had been volunteered to assist in a demonstration.

And then Dario had stripped to reveal the lacy underthings beneath his well-tailored clothes and, well, it was too beautiful a sight not to get aroused while further adorning him with ropes.

And Chris, devious bastard that he was, dictated an arrangement of those ropes that left Dario quite fuckable. Wearing that gorgeous red robe of his, he leaned against the wall, all but openly drooling as he gave stern orders on first the placement of the ropes, then hands, then mouth, then cock.

By the time Santi cut Dario down, he had committed twice as many sins as the first time, and Dario was drunk with bliss, staring wide-eyed at them both and murmuring delightedly in Spanish.

His beautiful undergarments were hopelessly soaked with sweat and other fluids, so there was nothing to do but strip them off.

“Grab me a robe for him?” Santi asked while carefully maneuvering a shaved leg through delicate fabric.

Chris came around behind Dario, shrugging out of his robe. “He can have this one,” Chris said, gently draping the robe over the boy’s shoulders. “I won’t be needing it.”

“No?”

Chris grinned. “I do hope you haven’t exhausted yourself, my dear. Though I suppose I can enjoy you one way or the other. And after that demonstration, I do intend to enjoy you very thoroughly.”

Well. How could he possibly pass that up?

Together, they got the robe onto Dario and tucked their eager student into bed before heading for their own bedroom.

Santi was going to have an interesting visit to church in the morning.


	3. Dodging Hell on a Technicality

**Summary for the Chapter:**

> A minor sin inspired by the following lines from Ink and Bone:  
> “Maybe he’s giving a different service,” Dario said. “Have you finished licking our esteemed Scholar’s arse yet, or are you merely pausing for breath?”  
> “Sorry, was I taking your turn polishing his apples?”
> 
> Time for the usual barrage of warnings!  
> This is Jess fantasizing. Thus, I am not writing Jess/Dario/Wolfe actually happening. My only sin is describing a 16-year-old boy doing a thing that teenage boys do regularly while having what is likely a very common fantasy.
> 
> That said:  
> This is Jess/Dario/Wolfe.  
> There are descriptions of masturbation, rimming, and blowjobs.  
> Jess and Dario are 16-year-old students here. Wolfe is their 39-year old teacher. The power dynamics are totally fucked up.  
> Jess and Dario are providing sexual favors in exchange for better grades. Again, the power dynamics are totally fucked up.  
> Once again, since people can get upset about this sort of thing: Jess is 16. Dario is 16. If that bothers you, skip this one.  
> Read at your own risk.

Dario was out with his cronies. That meant Jess finally had the room to himself for a while. He could finally have a proper wank instead of furtively rubbing one out under the covers or in the shower.

And what fantasy did his brain supply him with once he got his cock in his hand? Not Khalila or any of the other perfectly attractive girls in the class. No, his mind fixated on Dario’s words from earlier about licking Scholar Wolfe’s arse. And his own response that Dario might be engaged in similar activities.

He pushed that aside and tried to picture Khalila stripping while he started to stroke himself.

No good. All he could see was Scholar Wolfe, standing behind his desk and glaring at Jess as he stood in the doorway of Wolfe’s office.

“Come in, Brightwell,” Wolfe said, impatient.

“Yes, sir.” Jess entered and shut the door.

“You know why you’re here, don’t you?”

Jess felt the blood rising to his cheeks not only in his fantasy, but also in reality. He shouldn’t even be thinking about Wolfe this way, but…

“Yes, sir. Please, sir, I’ll do anything to bring my grades up.”

“Good. Strip. I want you over here on your knees. Be quick about it.”

Jess got his clothes off far more quickly in his imagination than he possibly could have stripped in reality. It probably helped that his fantasy self wasn’t wearing a smuggling harness.

As he approached the desk, he could hear a soft slurping sound. Then he got around the desk and stopped short. Scholar Wolfe was naked from the waist down, and he had a larger cock than Jess had ever seen. He’d expected his perverted imagination to give him that. But he also saw Dario Santiago, stripped bare, kneeling before Wolfe and licking the Scholar’s balls. Dario’s cock, as gorgeous as the rest of him, was hard and dripping.

Jess felt a few drips of semen on his hand as he let his mind linger on that image.

“Behind me, Brightwell,” Wolfe said. “I think you already know what service I require of you.”

Jess dropped to his knees behind Wolfe, ducking under his instructor’s Scholar’s robe to face the man’s arse. He was all lean muscle, firm and tight. A runner’s body, what Jess might hope his own would look like when he’d matured.

He put his hands on those firm arse cheeks and spread them, kissing each cheek as he did.

“Get on with it, Brightwell. Earn those grades you want so badly but can’t be bothered to study for.”

“Yes, sir.”

He ran his tongue along the length of the Scholar’s crack. It was smooth and hairless, and it tasted like the hand he’d shoved into his mouth in reality to muffle the moan that threatened to escape him. He didn’t trust the walls of Ptolemy House to be thick enough to prevent the sound from carrying.

“Good boy,” Wolfe said, but not to Jess. Around the other side, Dario had shifted position, and by the sound of his muffled moans, he was trying to take Wolfe’s whole cock into his mouth.

The thought of Dario choking on Wolfe’s cock was enough to make Jess tighten his fist around his cock and quicken the pace of his jerking.

“Brightwell. Focus on your own task.”

Chastened, he focused his attention on the tight circle of Wolfe’s arsehole, tracing it with his tongue a few times before hesitantly pushing inward. The inside was hot and soft, and Jess pumped his tongue in and out in time with the motion of his real wanking.

He was probably supposed to be finding Wolfe’s prostate. He had no idea how to go about that, so he imagined himself a way out. A very appealing way out as he began to think of it.

“That will be enough of that, Brightwell,” Wolfe said, sounding entirely too calm for a man having both his cock and his arse licked. “Santiago appears to need your assistance. Go and help him before he embarrasses himself too badly with this pathetic performance.”

Jess moved around to kneel beside Dario, who had his mouth on the tip of Wolfe’s cock. Jess leaned in to join him, wrapping his lips around the side of the Scholar’s thick shaft. His mouth slid upward, Dario’s downward, until their lips met, as if they were kissing. He felt Dario’s tongue on his as they wrapped their lips around Wolfe’s head together.

He reached for Dario’s cock. Dario reached for Jess’s. Wolfe’s stern voice made both their hands freeze, even as Jess’s real hand increased its pace. “Focus. Both of you. You can play with each other on your own time. Brightwell, let’s see if you can show Santiago how it’s done. Santiago, attend to my balls.”

Their mouths slid past each other until the head of Wolfe’s cock was pushing past Jess’s lips while Dario dropped to lick Wolfe’s balls again. Inch by inch, Wolfe pushed his way into Jess’s mouth.

“Take it all, Brightwell. You _can_ do better than Santiago, can’t you?”

Of course he could. Jess’s hand was moving as fast as it could go, now, as he imagined how Wolfe’s cock would feel pressed against the back of his throat. It would be like swallowing a key. He could do it.

Wolfe moaned with the pleasure of Jess’s efforts. In reality, Jess bit down on the hand in his mouth to keep himself quiet. 

“Well done, Brightwell. Back up now, both of you. Focus on the head. Finish the job well and you’ll both get your passing grades.”

Jess felt his orgasm coming as he imagined himself and Dario licking Wolfe’s head together while the Scholar wrapped a hand around the base of his own shaft to push himself over the edge. Imaginary Wolfe came at the same time Jess did, and the waves of Jess’s climax crashed through him as he pictured himself and Dario licking up Wolfe’s come together. It hadn’t all made it into their mouths, and Jess understood before Wolfe even said anything that he and Dario were to lick each other’s faces clean.

Taking the hand from his mouth, Jess replaced it with his other, wetter hand so he could lick himself clean, still half in the fantasy and imagining it was Wolfe’s mess he was cleaning from Dario’s impossibly good-looking face.

As Jess let out a satisfied sigh, imaginary Wolfe said, “Good boys. You have earned your grades. Since you’ve pleased me, I will allow you to attend to each other now.”

Jess groaned, pushing himself upright to go and find clean pajamas. As his arousal faded, shame was beginning to creep in. Still, he had a sinking feeling that he already knew what he would be thinking of the next time he jerked off.


End file.
